GB763041A - New pyrimidine derivatives - Google Patents

New pyrimidine derivatives

Info

Publication number
GB763041A
GB763041A GB978252A GB978252A GB763041A GB 763041 A GB763041 A GB 763041A GB 978252 A GB978252 A GB 978252A GB 978252 A GB978252 A GB 978252A GB 763041 A GB763041 A GB 763041A
Authority
GB
United Kingdom
Prior art keywords
dimethylamino
chloro
chlorobenzeneazo
chloropyrimidine
methylamino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB978252A
Inventor
William Robert Boon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB978252A priority Critical patent/GB763041A/en
Publication of GB763041A publication Critical patent/GB763041A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
    • C09B62/24—Azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises pyrimidine derivatives of the general formula <FORM:0763041/IV(b)/1> in which Ar is an aryl radical which may optionally bear substituents, X is hydrogen or a lower alkyl radical, Y is a lower alkyl radical or X and Y together with the adjacent nitrogen atom form a heterocyclic ring, and Z is hydroxyl, amino, the group NX1Y1 (wherein X1 is hydrogen or a lower alkyl radical and Y1 is a lower alkyl radical), or the group NH-CRR11-COR1 (wherein R is hydrogen and R11 is hydrogen, phenyl or halophenyl radical and wherein R1 is phenyl or lower alkyl or alkoxy radical), provided that of the groups NXY and Z at least one is the residue of a secondary amine. The terms "lower alkyl" and "alkoxy" include up to 6 and 4 carbon atoms respectively. They are prepared by reacting a compound of the formula <FORM:0763041/IV(b)/2> with an aryldiazonium salt. The following examples are given: (1) dimethylguanidine sulphate is heated with sodium methoxide and then with diethyl malonate to give 2-dimethylamino-4,6-dihydroxypyrimidine, which is treated with phosphorus oxychloride to give 2-dimethylamino - 4,6 - dichloropyrimidine which, by heating with alcoholic ammonia is converted to 2-dimethylamino - 4 - amino - 6 - chloropyrimidine; the latter compound is then coupled with diazotized p-chloroaniline to yield 2-dimethyl-amino - 4 - amino - 5 - p - chlorobenzeneazo - 6-chloropyrimidine. (2) 2-Dimethylamino-4-methylamino - 6 - chloropyrimidine obtained by heating 2 - dimethylamino - 4,6 - dichloropyrimidine with alcoholic methylamine is coupled with diazotized p-chloroaniline to yield 2 - dimethylamino - 4 - methylamino - 5 - p-chlorobenzeneazo - 6 - chloropyrimidine. (3) By a similar process there are obtained 2,4-bis (dimethylamino) - 6 - chloropyrimidine and 2,4-bis(dimethylamino) - 5 - p - chlorobenzeneazo-6-chloropyrimidine. (4) Desylamine is reacted with trichloropyrimidine to give 2,4 - dichloro-6-desylaminopyrimidine which is heated with alcoholic dimethylamine to give 4-chloro-6-desylamino - 2 - dimethylaminopyrimidine and coupled with diazotized p-chloroaniline to yield 4 - chloro - p - chlorobenzeneazo - 6 - desylamino - 2 - dimethylaminopyrimidine; by similar methods a - (p - chlorophenyl) - a (4-chloro - 5 - p - chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylamino) - acetophenone is obtained from a - amino - a - (p - chlorophenyl)-acetophenone, the latter compound being prepared by treating p-chlorobenzylphenyl ketone with butyl nitrite and acid, and reducing the a - nitroso - p - chlorobenzylphenyl ketone so formed with hydrogen and palladized charcoal. In examples there are obtained by similar processes (5) ethyl 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylaminoacetate from ethyl 4-chloro-2-dimethylamino-6-pyrimidylaminoacetate (obtained by heating 4, 6-dichloro-2-dimethylaminopyrimidine with glycine ethyl ester), (6) 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - hydroxypyrimidine from 4 - chloro - 2 - dimethylamino - 6 - hydroxypyrimidine (obtained by heating 4-chloro-2-dimethylamino - 6 - methoxypyrimidine with hydrochloric acid); (7) 4 - chloro - 5 - -p chlorobenzeneazo - 2 - diethylamino - 6 - methylaminopyrimidine and 4 - chloro - 5 - p - chlorobenzeneazo - 6 - methylamino - 2 - piperidinopyrimidine; and (8) 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylaminoacetone starting from trichloropyrimidine and aminoacetone semicarbazone. The preparation of 2 - dimethylamino - 4 - methylamino - 5 - benzeneazo - 6 - chloropyrimidine, 2 - dimethylamino - 4 - methylamino - 5 - o-methoxybenzeneazo - 6 - chloropyrimidine, 2-dimethylamino - 4 - methylamino - 5 - p - nitrobenzeneazo - 6 - chloropyrimidine and 2 - dimethylamino - 4 - methylamino - 5 - a - naphthaleneazo - 6 - chloropyrimidine also is described. Specifications 763,042, 763,044 and 763,120 are referred to. According to the Provisional Specification the above defined alkyl and alkoxy groups may be replaced by any hydrocarbon groups.
GB978252A 1952-04-18 1952-04-18 New pyrimidine derivatives Expired GB763041A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB978252A GB763041A (en) 1952-04-18 1952-04-18 New pyrimidine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB978252A GB763041A (en) 1952-04-18 1952-04-18 New pyrimidine derivatives

Publications (1)

Publication Number Publication Date
GB763041A true GB763041A (en) 1956-12-05

Family

ID=9878656

Family Applications (1)

Application Number Title Priority Date Filing Date
GB978252A Expired GB763041A (en) 1952-04-18 1952-04-18 New pyrimidine derivatives

Country Status (1)

Country Link
GB (1) GB763041A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259623A (en) * 1963-06-14 1966-07-05 Olin Mathieson Process for preparing 2-(secondary amino)-halogenopyrimidines
US7816353B2 (en) * 2003-10-24 2010-10-19 Exelixis, Inc. P70S6 kinase modulators and method of use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259623A (en) * 1963-06-14 1966-07-05 Olin Mathieson Process for preparing 2-(secondary amino)-halogenopyrimidines
US7816353B2 (en) * 2003-10-24 2010-10-19 Exelixis, Inc. P70S6 kinase modulators and method of use

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